O'Neil Property Group
The original Sleepy Hollow — Floyd Falese’s 1950s plan of winding roads around three lakes, with ranches, split-levels, and custom homes on wooded half-acre-plus lots and no HOA.
Sleepy Hollow Manor is where the village began. Developer Floyd T. Falese bought Sleepy Hollow Farm in 1953 and laid out the Manor’s winding roads and cul-de-sacs to follow the land—around the trees, along the contours, and past the three lakes (Paula, Sharon, and Ichabod) that still anchor the neighborhood. The street names carry the Washington Irving theme: Winmoor Drive, Joy Lane, Glen Oak, Hemlock, Willow. Homes went up from the late 1950s onward, and scattered infill and custom rebuilds have continued into recent years, which is why MLS-fed sources show build years spanning the 1950s to the 2020s.
The housing stock is the most varied in the village: original ranches and split-levels, expanded mid-century homes, and one-off custom builds, running from about 1,600 to more than 5,000 square feet. Lots average roughly a half acre—many larger—and there is no homeowners association. Recent sales have ranged from about $415K for original-condition homes to $635K for updated or larger properties, with yearly medians in the $420Ks–$460Ks since 2023. Average property taxes run in the low-to-mid $7,000s, the lowest of the village’s neighborhoods.
What the Manor offers that the village’s later subdivisions can’t is the setting itself: lake-view and lake-adjacent lots, mature oak canopy, and the short walk to Sabatino Park, where the village’s Fourth of July festival and Halloween in the Hollow happen every year. Sleepy Hollow Elementary and the Dundee Township Park District’s Sleepy Hollow Center on Winmoor Drive both sit within the neighborhood’s orbit. For buyers who want character and land over uniform finishes, this is the first place I show.
Pricing reflects Sleepy Hollow Manor sales and MLS-fed sources as of summer 2026.
Ranches and split-levels from the neighborhood’s first decades, many with original kitchens, baths, or mechanicals priced accordingly. These are the village’s best value plays — a half-acre wooded lot with a clear renovation path to mid-$500s value.
See listings →Renovated mid-century homes and larger customs, often with lake views, finished lower levels, and modern kitchens. This is where most Manor sales have landed since 2024, and well-presented homes here have closed above list.
See listings →Lake-lot homes and 2000s–2020s infill builds list a few times a year and draw immediate attention. If you want water or newer construction inside the original neighborhood, get on our alert list — these rarely wait for a second weekend.
See listings →Sleepy Hollow Manor listings appear within the full Sleepy Hollow search — inventory here is a handful of homes a year, so tell us if you want alerts the day one hits.
Lakes Paula, Sharon, and Ichabod thread through the Manor — some homes front the water, many more have views or short walks to it. Waterfront turnover is rare and priced accordingly.
Larry Sabatino Memorial Park — playground updated in 2023 — hosts the Fourth of July festival (fun-run, parade, car show, fireworks) and Halloween in the Hollow (hayrides, chili contest, bonfire).
The Dundee Township Park District facility on Winmoor Drive adds tennis, basketball, sand volleyball courts, a playground, and a preschool — walkable from much of the neighborhood.
Falese’s plan built around the trees, not through them. Sixty-plus years later the Manor’s oak canopy and low-traffic curving streets are its defining feature — and unreproducible in newer construction.
Sleepy Hollow Manor is served by Community Unit School District 300. Verify current attendance boundaries with the district, as they can change.
The village’s own elementary school, located inside Sleepy Hollow. Confirm the current attendance boundary with District 300 for any specific address.
Located in West Dundee, serving Sleepy Hollow and the surrounding Dundee-area communities; district bus service covers the village.
The area’s comprehensive high school, located in Carpentersville, with academic, athletic, arts, and career-technical programs.
Sabatino Park, Sleepy Hollow Elementary, and the Sleepy Hollow Center are all inside or beside the neighborhood. There’s no commercial inside the village — groceries and retail are about ten minutes away on Randall Road, with downtown West Dundee and East Dundee’s riverfront dining just east.
Route 72 and Randall Road frame the village; Randall runs south to the I-90 interchange in about ten minutes. O’Hare is roughly 35–40 minutes via I-90 and the Loop about 40 miles east. Elgin’s employers and Advocate Sherman Hospital are about ten minutes south.
The Metra Milwaukee District West line’s Big Timber Road station in Elgin is about a ten-minute drive, with runs to Union Station in roughly 65–75 minutes; downtown Elgin stations add express options.
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